The cooperation of both the Medici and the Society of Jesus were necessary in the creation of the colleges; neither could have succeeded alone. Once founded, however, was that same cooperation between church and state also necessary for maintenance? The costs of the alliance with power could be high, but a lack of alliance might be costlier still. I shall explore the delicate, yet extremely important, developments in this relationship in Montepulciano and Florence during the seventeenth century, noting the impact of cooperation on both the Medici and the Jesuits in the areas of teaching and books along with property ownership and location, to determine whether or not the priests and politicians continued to work together to build a Medici Tuscany which was also a bastion of the Catholic Reform.